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14-hydroxy-11,13-dihydrohypocretenoldi-beta-D-glucopyranoside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](OCC2=C3C(=O)C=C([C@]43C[C@@H](CC2)[C@H](C(=O)O4)C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H28O9/c1-9-5-13(23)15-12(4-3-11-6-21(9,15)30-19(27)10(11)2)8-28-20-18(26)17(25)16(24)14(7-22)29-20/h5,10-11,14,16-18,20,22,24-26H,3-4,6-8H2,1-2H3/t10-,11-,14-,16-,17+,18-,20-,21+/m1/s1 |
| InChIKey | VGTGZABKFYVGPL-KELBHJMGSA-N |
| Formula | C21H28O9 |
| HBA | 9 |
| HBD | 4 |
| MW | 424.45 |
| Rotatable Bonds | 4 |
| TPSA | 142.75 |
| LogP | -0.64 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.71 |
| Exact Mass | 424.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Hedypnois cretica | Asteraceae | Plantae | 268036 |
Showing of synonyms
14-hydroxy-11,13-dihydrohypocretenoldi-beta-D-glucopyranoside
- Harraz FM, Kassem FF, et al. (1988). Hypnocretenolide derivatives from Hedypnois cretica. Phytochemistry,1988,27,6,1866-1867. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OCC(=C(C234)C(=O)C=C2)CCC(C3)CC(=O)O4
Level: 1
Mol. Weight: 424.45 g/mol
SMILES: C1=CC(=O)C(C123)=CCCC(C2)CC(=O)O3
Level: 0
Mol. Weight: 424.45 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 424.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.23
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.900
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.46
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.740
- Plasma Protein Binding
- 61.76
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.550
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.820
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.650
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.690
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -30.490
- Rat (Acute)
- 3.170
- Rat (Chronic Oral)
- 3.260
- Fathead Minnow
- 3.910
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 492.510
- Hydration Free Energy
- -7.170
- Log(D) at pH=7.4
- 0.460
- Log(P)
- -0.37
- Log S
- -1.71
- Log(Vapor Pressure)
- -12.41
- Melting Point
- 171.55
- pKa Acid
- 5.95
- pKa Basic
- 5.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7533 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7533 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7528 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7528 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7420 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7420 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7269 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7269 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7250 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7250 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7188 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7188 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7056 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7056 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7034 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7034 |